216871-75-9

Upstream product

• 6612-63-1 benzyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside 
• 100-53-8 phenylmethanethiol 
• 83-87-4 D-glucose pentaacetate 
• 604-69-3 β-D-glucose pentaacetate 
• 604-68-2 α-D-glucopyranose peracetylate 

Downstream Products

• 437758-21-9 benzyl S,S-dioxo-1-thio-β-D-glucopyranoside 
• 216871-80-6 benzyl S,S-dioxo-1-thio-2,3,4,6-tetra-O-(tert-butyldimethylsilyl)-β-D-glucopyranoside 
• 216871-85-1 (2R,3R,4S,5R)-3,4,5-Tris-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran 
• 216871-90-8 (2R,3S,4S,5R)-2-Hydroxymethyl-6-[1-phenyl-meth-(Z)-ylidene]-tetrahydro-pyran-3,4,5-triol 

Relevant academic research and scientific papers

Urea–hydrogen peroxide prompted the selective and controlled oxidation of thioglycosides into sulfoxides and sulfones

A practical method for the selective and controlled oxidation of thioglycosides to corresponding glycosyl sulfoxides and sulfones is reported using urea–hydrogen peroxide (UHP). A wide range of glycosyl sulfoxides are selectively achieved using 1.5 equiv of UHP at 60 °C while corresponding sulfones are achieved using 2.5 equiv of UHP at 80 °C in acetic acid. Remarkably, oxidation susceptible olefin functional groups were found to be stable during the oxidation of sulfide.

Application of HOF·CH3CN to the synthesis of glycosyl sulfones

A fast, complete and clean conversion of thioglycosides into glycosyl sulfones under mild acidic conditions is described, using the HOF·CH3CN complex at room temperature. This methodology affords glycosyl sulfones in high yields and in excellent purity.

A new route to exo-glycals using the Ramberg-Baecklund rearrangement

A new route to exo-glycals 4 is described in which glycosyl sulfones 3 are subjected to the Meyers variant of the Ramberg-Baecklund rearrangement. The conversion of sulfones derived from glucose, galactose, mannose, cellobiose, and ribose into di-, tri-, and tetra-substituted alkenes is reported. Preliminary mechanistic studies of this process are also described. Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002.

Synthetic applications of Ramberg-Backlund derived exo-glycals

Synthetic applications of the title glycals, prepared from S-glycoside dioxides using the Meyers' variant of the Ramberg-Backlund rearrangement are described. These include a formal total synthesis of a novel β-glycosidase inhibitor, and an efficient route to spirocyclic glucose derivatives. In addition, silyl methodology has been developed which allows unprotected exo- glycals to be synthesised.